This invention relates to heterocyclic carbothioamides. More particularly, this invention relates to 2-substituted-N-(3-substituted phenyl)thiazolidine-, tetrahydro-2H-1,3-thiazine-, and benzothiazoline-3-carbothioamides which are useful as insecticides.
Compounds containing the thiazolidine nucleus are not new; see, e.g., G. W. Stacy et al., J. Org. Chem., 23, 1760 (1958). Most of the 2-substituted thiazolidines appear to be 2-iminothiazolidines. The non-imino compounds, on the other hand, are primarily 2-thioureido-2-thiazolines. See, for example, E. Cherbuliez et al., Helv. Chim. Acta, 49, 807 (1966) [Chem. Abstr., 64, 158664d (1966)]; Y. Yamamoto et al., Kyoritsu Yakka Daigaku Kerkyu Nempo, 1973, 53 [Chem. Abstr., 81, 136039z (1974)]; D. L. Klayman et al., Tetrahedron Lett., 1967, 281 [Chem. Abstr., 66., 94943x (1967)]; D. L. Klayman et al., J. Heterocycl. Chem., 5, 517 (1968); S. P. Kharida et al., J. Indian Chem. Soc., 37, 305 (1960) [Chem. Abstr., 55, 10373a (1961)]; and D. L. Klayman et al., Tetrahedron, 25, 191 (1969). No utilities appear to have been disclosed for any of such compounds.
T. P. Forrest et al., Can. J. Chem., 52, 2725 (1974), disclose 5-methoxy-2-phenylamino-2-thiazoline and 2-(1,3-diphenylthioureido)-5-methoxy-2-thiazoline. Again, no utilities are disclosed. Finally, R. E. Hackler et al., Synthetic Communications, 5, 143 (1975), disclose the formation of 2-substituted-2-thiazolines from haloalkyl isothiocyanates. Examples of such 2-substituents include dimethylamino, piperidino, and 4-methylpiperidino. No utilities were given.